(2R,3R,4R,5S)-2-(hydroxymethyl)-1-[6-(2,2,2-trifluoroethoxy)hexyl]piperidine-3,4,5-triol

• ChemBase ID: 175899
• Molecular Formular: C14H26F3NO5
• Molecular Mass: 345.3551496
• Monoisotopic Mass: 345.1763076
• SMILES: [C@@H]1([C@@H]([C@@H](CN([C@H]1CO)CCCCCCOCC(F)(F)F)O)O)O
• Canonical SMILES: OC[C@@H]1N(CCCCCCOCC(F)(F)F)C[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C14H26F3NO5/c15-14(16,17)9-23-6-4-2-1-3-5-18-7-11(20)13(22)12(21)10(18)8-19/h10-13,19-22H,1-9H2/t10-,11+,12-,13-/m1/s1
• InChIKey: XZWXZUXXANFWSU-YVECIDJPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5S)-2-(hydroxymethyl)-1-[6-(2,2,2-trifluoroethoxy)hexyl]piperidine-3,4,5-triol
• IUPAC Traditional name: (2R,3R,4R,5S)-2-(hydroxymethyl)-1-[6-(2,2,2-trifluoroethoxy)hexyl]piperidine-3,4,5-triol
• Synonyms: (2R,3R,4R,5S)-2-(Hydroxymethyl)-1-[6-(2,2,2-trifluoroethoxy)hexyl]-3,4,5-piperidinetriol; N-(7-Oxa-9,9,9-trifluorononyl)deoxynojirimycin

Database IDs

• CAS Number: 383417-50-3
• PubChem SID: 164231809
• PubChem CID: 49759798

CALCULATED PROPERTIES

• Acid pKa: 12.902188
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -2.9040563
• LogD (pH = 7.4): -1.137232
• Log P: -0.12811477
• Molar Refractivity: 77.0747 cm^3
• Polarizability: 30.013172 Å^3
• Polar Surface Area: 93.39 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: Off-White Amorphorous Solid

Safety Information

• Storage Condition: Hygroscopic, Store under Inert atmosphere Refrigerator

DETAILS

Toronto Research Chemicals - O845150

A inhibitor of glucosidase 1.

REFERENCES

• L.A.G.M., van den Broek, et al.: Reel. Trav. Chim. Pays-Bas, 112, 82 (1993)
• L.A.G.M., van den Broek, et al.: Reel. Trav. Chim. Pays-Bas, 113, 507 (1994)